Beat room-temperature cream cheese in a large bowl using a hand mixer until completely smooth and fluffy. Gradually add sifted powdered sugar, mixing until fully incorporated and lump-free. Pour in the whole milk and vanilla extract, then continue mixing until the filling has a smooth, pourable consistency without any lumps. Room temperature cream cheese is crucial to achieve the silkiest texture without graininess.

Gently add the thawed whipped topping to your cream cheese mixture. Using a silicone spatula, carefully fold the whipped topping into the mixture with light, sweeping motions to maintain as much air as possible. Continue folding until just combined and the mixture looks light and airy. Be careful not to overmix, as this will deflate the filling and compromise the cloud-like texture that makes this dessert special.

Create a beautiful layered presentation in either a trifle dish, 9×13-inch baking dish, glass bowl, or individual parfait glasses. Start by spreading half of the torn angel food cake pieces evenly across the bottom of your chosen container. Carefully spoon half of the cream mixture over the cake, spreading gently without pressing down too firmly. Next, distribute half of the cherry pie filling over the cream layer. Repeat the layering with remaining cake pieces, followed by the rest of the cream mixture, and finish with the remaining cherry pie filling on top for a stunning red and white display.

Place the assembled dessert in the refrigerator for at least 2 hours, though overnight chilling produces the best results. This resting time allows the flavors to meld together, the layers to set properly, and the cake to soften slightly as it absorbs moisture from the surrounding ingredients. The texture improves significantly after several hours of chilling, creating a perfectly cohesive dessert experience.